Development and Application of a Multielectron-Accepting Organic Oxidant for the Catalytic Transition-Metal-Free Oxidative Homocoupling of Grignard Reagents in Air

Korenaga, Toshinobu; Nitatori, Kaoru; Muraoka, Hiroki; Ogawa, Satoshi; Shimada, Kazuaki

Development and Application of a Multielectron-Accepting Organic Oxidant for the Catalytic Transition-Metal-Free Oxidative Homocoupling of Grignard Reagents in Air

2015

Korenaga, Toshinobu | Nitatori, Kaoru | Muraoka, Hiroki | Ogawa, Satoshi | Shimada, Kazuaki

Heptafluorotolyl-substituted perfluorocyclopentene acts as a four-electron oxidant for the homocoupling of Grignard reagents. It can also be used for catalytic homocoupling with a low catalyst loading (up to 2 mol %) in the presence of atmospheric oxygen. The organocatalytic cycle involves the generation of an organic radical and a perfluorocyclopentadienyl anion.

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